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$575,000
3 Beds 180189 MLS
Tucked into the High Country Subdivision outside Deadwood, this 3-bedroom, 2-bath Black Hills getaway sits on a 1.03-acre wooded lot with easy access off Hwy 385 via Brownsville Rd, perfect for year-round Black Hills adventure. Inside, you’ll feel the “cabin cozy” right away, made even better by major, thoughtful upgrades. The owners invested in a substantial addition adding 2 bedrooms + an additional full bath, and the convenience of a second laundry set, ideal for quick turnovers when the home is rented. For comfort in every season, enjoy the ambiance of a pellet stove alongside electric heat. Outside this cabin continues to shine: unwind in the hot tub on the patio, or stash all the gear in the large shed, and head out for the lifestyle the Northern Hills are known for. The Brownsville area is known for easy access to nearby trail systems and covenant free setting. You'll enjoy hunting, trail riding, snowmobiling, and easy drives to the best of the Black Hills.

21621 High Country Loop, Deadwood

$575,000
3 Beds 2 Baths 89642 MLS
Tucked into the High Country Subdivision outside Deadwood, this 3-bedroom, 2-bath Black Hills getaway sits on a 1.03-acre wooded lot with easy access off Hwy 385 via Brownsville Rd, perfect for year-round Black Hills adventure. Inside, you’ll feel the “cabin cozy” right away, made even better by major, thoughtful upgrades. The owners invested in a substantial addition adding 2 bedrooms + an additional full bath, and the convenience of a second laundry set, ideal for quick turnovers when the home is rented. For comfort in every season, enjoy the ambiance of a pellet stove alongside electric heat. Outside this cabin continues to shine: unwind in the hot tub on the patio, or stash all the gear in the large shed, and head out for the lifestyle the Northern Hills are known for. The Brownsville area is known for easy access to nearby trail systems and covenant free setting. You'll enjoy hunting, trail riding, snowmobiling, and easy drives to the best of the Black Hills.

21621 High Country Loop, Deadwood

$709,000
180160 MLS
Discover the perfect blend of historic charm and modern convenience in this unique Deadwood property! Situated on three commercially zoned lots just blocks from historic Downtown Deadwood, this beautifully restored home offers timeless character with extensive modern updates. Originally located on Lower Main Street, the home was carefully relocated in 2015 and placed on a new foundation at its current location in 2016. Offering 4 bedrooms and 4-1/2 bathrooms, the spacious layout provides privacy and flexibility for a variety of living or business needs. Major improvements completed in 2016 include a new foundation, exterior restoration, updated electrical and plumbing systems, HVAC, and thoughtfully renovated interior spaces - preserving the home's historic appeal while incorporating today's conveniences. Opportunities to own a piece of Deadwood history with this level of modernization are rare. Whether you're searching for a distinctive residence, employee housing, office or business space, or an addition to your real estate portfolio, this exceptional property is one you won't want to miss. Listed by Jana Carlyle, 605-381-0909, The Real Estate Group.

21 Charles, Deadwood

$545,000
4 Beds 3 Baths 89486 MLS
Listed by Denise Gienger, Keller Williams Realty BH, 605-645-8496. First time ever offered for sale! Lovingly maintained by its original owners since 1979, this spacious home offers 3000 sq ft in one of Deadwood's established neighborhoods. The oversized kitchen is the heart of the home, offering abundant cabinetry, generous counter space, a bar for extra seating and a built-in desk. Just beyond, the unique two-level sunroom provides the perfect place to enjoy your morning coffee, soak in a hot tub, or unwind with a good book. The upper level features 3 beds and 2 baths including the spacious primary suite which a true retreat! The primary suite has two walk-in closets, an adjoining flex space that's perfect for a nursery, sitting room or private workout area and has a beautifully remodeled en-suite bath featuring a custom tiled walk-in shower. The .53-acre lot provides a beautiful setting with mature surroundings. Built with quality and cared for over the years, this home is ready for its next owners to enjoy for years to come.

4 Ryan Road, Deadwood

$291,000
2 Beds 1 Baths 89244 MLS
Some homes tell a story, and 8 Jefferson Street is one of them. Contact Cher Rhoades @ Oak & Key Realty 605.639.1158 for a Private Tour! Nestled in one of Deadwood's most iconic and historic neighborhoods, this charming 2-bedroom, 1-bath home has been lovingly cared for and stands as a true historical treasure. Built in 1933, the home is surrounded by stately historic residences, mature trees, and lush natural landscaping that create a peaceful setting just moments from the heart of town. In a community known for legends, history, adventure, and breathtaking hillside views, this timeless home offers a rare opportunity to own a piece of Deadwood's rich heritage. The character and craftsmanship of a bygone era remain evident throughout, while years of thoughtful care have ensured the home is move-in ready for its next owner. Tucked away among the trees, this inviting property features warm, welcoming spaces, charming windows that fill the home with natural light, two comfortable bedrooms, one bathroom, and a detached one-car garage. Its timeless appeal captures the spirit of Deadwood's past while offering the comfort and convenience of today. Whether you're searching for a full-time residence, a Black Hills retreat, or simply a home with a story worth continuing, 8 Jefferson Street is ready for its next chapter. Come experience the character, history, and charm that make this home truly unforgettable.

8 Jefferson Street, Deadwood

$291,000
2 Beds 179696 MLS
Some homes tell a story, and 8 Jefferson Street is one of them. Contact Cher Rhoades @ Oak & Key Realty 605.639.1158 for a Private Tour! Nestled in one of Deadwood's most iconic and historic neighborhoods, this charming 2-bedroom, 1-bath home has been lovingly cared for and stands as a true historical treasure. Built in 1933, the home is surrounded by stately historic residences, mature trees, and lush natural landscaping that create a peaceful setting just moments from the heart of town. In a community known for legends, history, adventure, and breathtaking hillside views, this timeless home offers a rare opportunity to own a piece of Deadwood's rich heritage. The character and craftsmanship of a bygone era remain evident throughout, while years of thoughtful care have ensured the home is move-in ready for its next owner. Tucked away among the trees, this inviting property features warm, welcoming spaces, charming windows that fill the home with natural light, two comfortable bedrooms, one bathroom, and a detached one-car garage. Its timeless appeal captures the spirit of Deadwood's past while offering the comfort and convenience of today. Whether you're searching for a full-time residence, a Black Hills retreat, or simply a home with a story worth continuing, 8 Jefferson Street is ready for its next chapter. Come experience the character, history, and charm that make this home truly unforgettable.

8 Jefferson 8 Jefferson Street, Deadwood

$499,500
3 Beds 3 Baths 89213 MLS
Welcome to your new home nestled in one of Deadwood’s most sought-after neighborhoods! This delightful single-family residence offers the perfect blend of comfortable living, entertaining spaces, and spectacular Black Hills vistas — all just minutes from historic Deadwood. With approximately 2,242 sq ft of well-designed living space, this three-bedroom, three-bath home was built in 1981 and thoughtfully maintained over the years. The open and inviting floor plan includes a cozy living area with a fireplace, ideal for relaxing evenings with family and friends. Large windows throughout the main level flood the space with natural light and showcase views of the surrounding hillsides. The heart of the home features a spacious kitchen with ample counter space and easy flow to adjacent living and dining areas — perfect for everyday living and entertaining. Step outside onto the generous deck to enjoy your morning coffee, host summer barbecues, or simply take in the fresh mountain air and scenic views. Situated in the beautiful Black Hills and served by the Lead-Deadwood school district, this property is ideally positioned for easy access to local amenities, outdoor recreation, and the vibrant community of Deadwood.

2 Ryan Road, Deadwood

$675,000
4 Beds 3 Baths 89058 MLS
Contact Matt Klein 605-920-1341 with Century 21 Associated Realty in Deadwood for showings and more information! Prime location on this Deadwood Main Street home with 4 bedrooms and 2.5 bathrooms just seconds from all the action downtown. The detached garage, off-street parking, and level street access with on-street parking in front is highly sought after. There's an 8000w Honda gas powered generator installed to keep you powered on through the weather. The main floor has a warm living room with tongue-and-groove wood accents, brick fireplace, and wood floors that flows to large open kitchen and dining area. The kitchen has an island, nice counters, and plenty of windowed views for natural lighting. There is a mud room off the kitchen that accesses the back partial covered deck and pathway to the detached garage. Also on the main floor there is a primary bedroom with ample closets and a private full bathroom. There is main floor laundry off the front door entryway with additional half-bathroom. The upper level has one bedroom with storage, an office loft area, and a large bonus storage room over the living areas. The walkout basement has a large game room with dry bar, 2 bedrooms, 1 bathroom, and a den/office area. The walkout from the basement flows onto a large deck that looks out on the lawn, mountainous views, andmature tree growth. The home has diamond cote manufactured siding, an impressive Bridger Steel 20-22 gauge (approx) metal roof, and a tankless water heater.

875 Main Street, Deadwood

$715,000
4 Beds 4 Baths 89051 MLS
Some homes offer just an address, but 152 Charles St. has a story to tell. Built circa 1890, this is one of Deadwood's most remarkable homes; a Folk Victorian farmhouse with a 1920s Arts & Crafts addition, fully restored to honor 135 years of history while delivering every modern comfort. Step through the reclaimed antique front door into 2,800+ square feet of thoughtfully remodeled living space across three levels. Restored wide-plank Douglas Fir hardwood floors, 9-foot ceilings, and a stunning staircase with hand-restored black walnut spindles. On the main floor, the show stopping kitchen, formal dining room, parlor and laundry anchor everyday life beautifully. The kitchen features custom cabinetry, Cambria countertops, and a culinary stove complete with a pasta arm. The fully finished basement with a full wet-bar, including a custom bar back, adds another dimension of living space. Out back, a sprawling deck nestles above Whitewood Creek, creating an outdoor experience unlike anything else. With a two vehicle car port, convenient access to Downtown and Deadwood trolley stops, this home is prime for classic Black Hills living. This stunning home has been restored and returned to the best version of herself. Every piece of furniture, fixture, and finish has been hand selected and curated to showcase this home from the Golden Age. Schedule your showing today. Listed by Madison (Reeves) Shipman, Valente Realty (605)569-9019

152 Charles Street, Deadwood

$1,690,000
179410 MLS
Listed by Daneen Jacquot Kulmala South Dakota Properties 605-484-7832 & Steve Kulmala South Dakota Properties 605-484-8501. If you are looking for an awesome investment property, look no further!! Six beautiful cabins in a great location, near Deadwood, Trails and lakes! These cabins stay busy year-round!! New well for Cabins 4, 5, 6 – $100,000. UV water filtration system for Cabins 1, 2, 3 – $12,000. Deck stairs for Cabins 2 and 3 – $5,000. Safety railings for Cabins 1, 3, 6 – $20,000+. New sofas in all cabins – $15,000. New gas ranges – $2,400. New dishwashers – $1,500. New shower installation – $1,500. New front doors – $2,100. New patio doors – $4,400. New windows – $1,500. New refrigerators – $3,400. Septic electrical repair – $3,000. Plumbing upgrades – $8,000. New hot water heaters Call today for your personal showing!!

21353-21361 Hwy 385 21353-21361 Hwy 385, Deadwood

$1,690,000
179409 MLS
Listed by Daneen Jacquot Kulmala South Dakota Properties 605-484-7832 & Steve Kulmala South Dakota Properties 605-484-8501. If you are looking for an awesome investment property, look no further!! Six beautiful cabins in a great location, near Deadwood, Trails and lakes! These cabins stay busy year-round!! New well for Cabins 4, 5, 6 – $100,000. UV water filtration system for Cabins 1, 2, 3 – $12,000. Deck stairs for Cabins 2 and 3 – $5,000. Safety railings for Cabins 1, 3, 6 – $20,000+. New sofas in all cabins – $15,000. New gas ranges – $2,400. New dishwashers – $1,500. New shower installation – $1,500. New front doors – $2,100. New patio doors – $4,400. New windows – $1,500. New refrigerators – $3,400. Septic electrical repair – $3,000. Plumbing upgrades – $8,000. New hot water heaters Call today for your personal showing!! With the right terms, the seller will consider contract for deed

21353-21361 Hwy 385 21353-21361 Hwy 385, Deadwood

$432,000
3 Beds 3 Baths 88867 MLS
A Rare Find in Deadwood call Greg Klein at Century 21 Associated Realty 605-920-1342 to see this fully updated 3 bedroom, 3 bath town home minutes from down town on a quiet corner lot with private deck. Walking distance to the Mickelson Trail, rec center, coffee shops, restaurants, and medical center. This home is spacious, bright and sunny. New appliances, quartz counter tops, vinyl plank flooring, gas fireplace warms living/dining area open to the kitchen as well. You will love recent high dollar upgrades like the stunning new oversized walk in master bath shower with show room quality tile and fixtures. Forced air natural gas heat and central air conditioning, two stall garage. Get away from it all in the downstairs rec room area and guest bedroom with 3/4 bath. Possible owner financing with 50% down.

6 Calamity Lane, Deadwood

$90,000
2 Beds 1 Baths 88836 MLS
Updated, Affordable Home Minutes from Downtown Deadwood! Ideally located just minutes from historic downtown Deadwood and the scenic Mickelson Trail, this well-maintained manufactured home offers an affordable opportunity to enjoy the best of the Black Hills. Recent updates include newer siding, a durable metal roof, upgraded water heater and thermostat, stylish vinyl plank flooring, modern light fixtures, and fresh window treatments. Whether you're looking for a full-time residence or a convenient getaway, this move-in-ready property combines comfort, value, and proximity to everything Deadwood has to offer. Contact Kristi Villafuerte at Black Mountain Real Estate (605) 591-2705 to schedule your private showing today!

200 Charles Street, Deadwood

$399,000
3 Beds 3 Baths 88779 MLS
Call Jordan Seibel (Oster) w/ Century 21 Associated Realty @ 307.290.0552 today for Location, Location, Location, And no covenants! This upgraded 3 bed, 3 bath sits right off Highway 385, one of the Black Hills most scenic drives! You are only minutes from Deadwood, or a beautiful cruise to Custer State Park, Crazy Horse and Mount Rushmore. Surrounded by tons of recreational trails, and just a cruise to the ski-slopes, or the lake! This spacious layout offers two fireplaces- one propane and one electric, big windows for lots of light, and all the unique accents add warmth throughout! The master provides built-in cabinetry adding more space, and the basement's ready to provide years of entertaining! Again, no covenants! And it has a private well!

21375 Highway 385, Deadwood

$799,000
4 Beds 179139 MLS
Welcome to Twin Pines Lodge — a truly unique and charming home perched on the slope of Mount Roosevelt with panoramic views of historic Deadwood. Just one block west of the iconic Franklin Hotel and steps from Outlaw Square, this property offers unbeatable proximity to the best of downtown. Recently refreshed with updated décor and thoughtfully selected finishes that perfectly complement the lodge-style character of the home, the interior blends rustic charm with a warm, inviting atmosphere. The home features 4 bedrooms and 3 bathrooms across a versatile layout and will be sold fully furnished, making it truly turnkey from day one. The lower level includes a full kitchen, living room, bedroom, and bathroom — ideal for extended guests, multigenerational living, a mother-in-law suite, or a private guest setup. The main level offers inviting living space and a spacious sunroom that’s perfect for relaxing or entertaining. A detached 2-car garage adds even more appeal with a finished loft above — ideal for a game room, office, or creative space. With its prime location, updated interior feel, flexible design, and turnkey convenience, Twin Pines Lodge is a rare opportunity to own a piece of Deadwood with character, comfort, and unmatched views.

10 Centennial, Deadwood

$799,000
4 Beds 3 Baths 88777 MLS
Welcome to Twin Pines Lodge — a truly unique and charming home perched on the slope of Mount Roosevelt with panoramic views of historic Deadwood. Just one block west of the iconic Franklin Hotel and steps from Outlaw Square, this property offers unbeatable proximity to the best of downtown. Recently refreshed with updated décor and thoughtfully selected finishes that perfectly complement the lodge-style character of the home, the interior blends rustic charm with a warm, inviting atmosphere. The home features 4 bedrooms and 3 bathrooms across a versatile layout and will be sold fully furnished, making it truly turnkey from day one. The lower level includes a full kitchen, living room, bedroom, and bathroom — ideal for extended guests, multigenerational living, a mother-in-law suite, or a private guest setup. The main level offers inviting living space and a spacious sunroom that’s perfect for relaxing or entertaining. A detached 2-car garage adds even more appeal with a finished loft above — ideal for a game room, office, or creative space. With its prime location, updated interior feel, flexible design, and turnkey convenience, Twin Pines Lodge is a rare opportunity to own a piece of Deadwood with character, comfort, and unmatched views.

10 Centennial Avenue, Deadwood

$535,000
3 Beds 179088 MLS
Perched on 7+ acres with breathtaking hillside views of Deadwood. This property includes an easy access 7,000 sqft separate lot for park that could be used to build a garage / shop or additional home. This one-of-a-kind historic property offers the perfect blend of character, comfort, and location. Entertain from the custom party deck complete with outdoor bar, all while taking in panoramic views. Walkable to everything Deadwood has to offer, including direct access to the famous Mickelson Trail. This beautifully updated 3-bedroom, 2-bath home features two spacious living areas, an open-concept kitchen, a huge primary en-suite, and two cozy wood stoves. Rich original woodwork preserves the home’s historic charm, while tasteful updates throughout provide modern convenience. Being sold fully turnkey furnished — right down to the barware — this property is ready to enjoy immediately as a personal retreat, vacation home, or investment opportunity. As featured in Better Homes & Gardens, this exceptional property has too many upgrades to list and is offered at the incredible price of $535,000.

29 & 19 Other Terrace Ave & Stewart St, Deadwood

$535,000
3 Beds 2 Baths 88734 MLS
For more information, please contact listing agents Michael Warwick 605-641-2569 Great Peaks Realty. Perched on 7+ acres with breathtaking hillside views of Deadwood. This property includes an easy access 7,000 sqft separate lot for park that could be used to build a garage / shop or additional home. This one-of-a-kind historic property offers the perfect blend of character, comfort, and location. Entertain from the custom party deck complete with outdoor bar, all while taking in panoramic views. Walkable to everything Deadwood has to offer, including direct access to the famous Mickelson Trail. This beautifully updated 3-bedroom, 2-bath home features two spacious living areas, an open-concept kitchen, a huge primary en-suite, and two cozy wood stoves. Rich original woodwork preserves the home’s historic charm, while tasteful updates throughout provide modern convenience. Being sold fully turnkey furnished — right down to the barware — this property is ready to enjoy immediately as a personal retreat, vacation home, or investment opportunity. As featured in Better Homes & Gardens, this exceptional property has too many upgrades to list and is offered at the incredible price of $535,000.

29 Terrace Ave, Deadwood

$2,990,000
179033 MLS
Deadwood’s #1 rated hotel on Google — and it’s for sale. The Cedar Wood Inn is a rare, turnkey boutique hospitality asset in the heart of Historic Deadwood, steps from the city’s world-famous casinos, restaurants, bars, live entertainment, and nightlife. Guests enjoy the full Deadwood experience by night and return to a beautifully landscaped, peaceful retreat by morning — a balance of access and escape that no new-build can replicate, and no competitor in this market can offer. 24 well-appointed guest rooms spanning queen, king, double, and premium suite configurations. A three-bedroom manager’s apartment connected directly to the front office — live on-site and operate the business with zero commute, or house your property manager just steps from the front desk. A four-stall garage at the rear of the property for equipment storage, vehicles, or premium covered parking during high-traffic events. A city trolley stop is positioned directly at your front door. The reputation arrives with the keys. Deadwood’s #1 rated on Google. Numerous awards across TripAdvisor, Booking.com, Expedia, and Hotels.com. Hundreds of verified five-star reviews. A deeply loyal guest base that returns every single season without prompting. Platform authority and algorithmic rankings that drive organic bookings without any paid advertising — and compound in value every single year you hold this remarkable asset. Within an hour: Mount Rushmore, Crazy Horse Memorial, Custer State Park, Jewel Cave National Monument, and Spearfish Canyon Scenic Byway. The Sturgis Motorcycle Rally is just minutes away. Exceptional year-round regional draw with consistent, year-round revenue potential. This is not a turnaround story. This is not a renovation project. This is a fully operating, award- winning, reputation-rich boutique inn with an irreplaceable downtown Deadwood location and everything a serious buyer needs already built. Listed by Josiah LaFrance with L'Avance Capital and Real Estate- 605-786-3098

103 Charles, Deadwood

$399,900
3 Beds 178838 MLS
Perched on 7+ acres with breathtaking hillside views of Deadwood, this one-of-a-kind historic property offers the perfect blend of character, comfort, and location. Entertain from the custom party deck complete with outdoor bar, all while taking in panoramic views. Walkable to everything Deadwood has to offer, including direct access to the famous Mickelson Trail. This beautifully updated 3-bedroom, 2-bath home features two spacious living areas, an open-concept kitchen, a huge primary en-suite, and two cozy wood stoves. Rich original woodwork preserves the home’s historic charm, while tasteful updates throughout provide modern convenience. Being sold fully turnkey furnished — right down to the barware — this property is ready to enjoy immediately as a personal retreat, vacation home, or investment opportunity. As featured in Better Homes & Gardens, this exceptional property has too many upgrades to list and is offered at the incredible price of $399,900.

29 Other Terrace Ave, Deadwood